Water → rac-(3R,4S)-1-benzylpyrrolidine-3,4-diol

HRID 1018061Notes

Reaction equation

HRID 1018061 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC(S(O)(=O)=[O:21])=CC=1.[OH2:24].C1C=C(Cl)C=C(C(OO)=O)C=1>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:24])[CH:10]([OH:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7400p-Chlorobenzenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 536645rac-(3R,4S)-1-benzylpyrrolidine-3,4-diolYield 86.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 46.2 g (0.24 mol) of p-chlorobenzenesulfonic acid (produced by Tokyo Chemical Industry Co., Ltd.), 15.0 g of water, and 60.0 g of acetone in a round flask reactor, 31.1 g (0.13 mol) of 70% m-CPBA (m-chloroperbenzoic acid produced by Tokyo Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 10 hours at 40° C. without irradiation by lamps. After completion, acetone was evaporated under reduced pressure, neutralized by NaOH (aq), and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 16.8 g of 1-benzyl-3,4-dihydroxypyrrolidine (yield 86.9%) was obtained.

Workup

  1. customto react for 10 hours at 40° C. without irradiation by lamps
  2. customAfter completion, acetone was evaporated under reduced pressure
  3. extractionextracted with toluene and water
  4. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9fb0b2d5527842f4a10443fb50e99125
Source dataset
uspto-grants-2002_11
Patent number
US06479668B1

Reaction notes

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